In a state this beautiful, there are endless Virginia road trip possibilities! If you’re a driving enthusiast, check out this road trip itinerary to Virginia State Route 16, also known as the Back of the Dragon. Start by exploring the vibrant city of Charlottesville, then head to Floyd for the legendary Friday Night Jamboree at the Floyd Country Store. Spend your Saturday riding the Back of the Dragon, one of the best driving roads in the Appalachian Mountains. Finally, wander through Wytheville and its great outdoors before heading home or toward your next adventure!

Virginia is a good place to visit for its rich history, warm hospitality, and epic scenic drives. Its many shareable experiences like wine tours and cozy accommodations are a big part of why, as the saying goes, Virginia is for lovers. Here’s a closer look at how to plan your own Virginia road trip to the Blue Ridge Mountains and the state’s southwest.

Presented in partnership with Virginia Tourism

Charlottesville and Southwest Virginia road trip route

We loved every minute of this road trip to the Back of the Dragon! There are many ways to approach Southwest Virginia. We’ll share it as we took it so you can customize it to your own needs.

We spent a full day on Wednesday traveling from the Greater Toronto Area across the Canada-USA border and five state lines to reach Virginia. At our first stop in Charlottesville, Virginia, we dedicated a day and a half to exploring the city and the surrounding Albemarle County. On Friday afternoon, we headed toward Floyd for the Friday Night Jamboree at the Floyd Country Store. An early departure allowed us to spend most of the day on Saturday riding the Back of the Dragon. Finally, we passed an afternoon, evening, and morning exploring Wytheville before turning back toward Toronto. (This did get us home very late. Consider spending an extra night or more to Wytheville so you don’t feel rushed.)

Charlottesville: Add a youthful and artsy vibe to your Virginia road trip

Charlottesville is a little out of the way from the rest of the stops on this Southwest Virginia road trip. However, we highly recommend paying Charlottesville a visit, whether it’s as part of this road trip or along a different route. There’s so much to do in and around the city, from touring the presidential estates at Thomas Jefferson’s Monticello and James Monroe’s Highland to wine touring, eating at an 18th-century tavern, visiting Virginia’s first immersive art museum, and much more!

Explore things to do in Charlottesville, Virginia, by clicking here >

Floyd: Dance the night away at the Friday Night Jamboree at the Floyd Country Store

Floyd, Virginia, may not be as famous as Nashville, but the beating heart of country music lives here! If you visit on any day but Monday, you can check out the Floyd Country Store. Grab some great Southern food and browse through the shop. Odds are good you’ll be able to catch some live music while you’re there. But if you can possibly do so, plan your schedule around the Friday Night Jamboree. It’s been happening every Friday night for the past 40 years, and it’s a bucket list experience we didn’t know we needed!

The evening starts with an hour of beautiful gospel music. The crowd is hushed and the mood is subdued as people take in the sublime harmonies.

And then the dance set begins, and the entire place erupts with energy and life! During upbeat songs, the dance floor fills to the brim with people. The air fills with the sounds of the fiddle and banjo, singing and laughter, and the clicking of country dance shoes on the hardwood floor. During the waltzes and two-steps, couples young and old dance cheek to cheek. If you try to stay on the sidelines, it won’t last long. A friendly local is almost certain to ask you for a dance!

This weekly event is something every visitor must experience. It’s good old-fashioned family fun that operates by granny’s rules: no alcohol, no smoking, and no cussing allowed! And thanks to the Floyd Country Store’s Handmade Music School, these traditions are being passed on to the next generation. This means the Friday Night Jamboree and other events like it will continue on for many years to come. It’s absolutely worth planning your itinerary around being in Floyd on a Friday night to see it for yourself.

Back of the Dragon: Experience one of Virginia’s best driving roads

Virginia State Route 16 is known as the Back of the Dragon. It’s a winding mountain road that runs between the towns of Tazewell and Marion through the Appalachians. There are 438 curves across its 32 miles, which trace up and down three different mountainsides. Because it’s a challenging and technical road that also offers scenic drives, it’s popular among driving and motorcycling enthusiasts.

We recommend dedicating at least six hours to your visit. This will give you enough time to complete two full round-trip runs on the road with appropriate time for breaks.

Learn more about how to plan your Back of the Dragon drive here >

Spend time in Wytheville to enjoy the great outdoors on a Virginia road trip

Whether you start or end your journey in Wytheville or you’re just passing through, you’ll be glad you did. Wytheville has plenty of great outdoor experiences to explore, from Virginia’s oldest and highest-elevation privately owned attraction to the 57.7-mile rail trail at New River Trail State Park and more. The town is so inviting and steeped in Southern charm, it’s well worth a visit.

Find six sensational things to do in Wytheville here >

Frequently asked questions (FAQs)

How long does it take to drive to Virginia from Ontario or Quebec?

To reach Charlottesville or Wytheville from most points in Southern Ontario, expect to spend nine and a half to ten hours on the road, not including stops or the border crossing. From Ottawa or Montreal, you’ll need 11 to 12 hours depending on your final destination. It does make for a long day, so it’s best to set aside a full day in either direction if you can or consider making a stopover on the way.

What is Virginia famous for?

Virginia is well-known for its rich history, more than 300 wineries, and spectacular scenery along the Blue Ridge Mountains. It’s a fantastic destination for a road trip.

What is the best season to visit Virginia?

Spring and fall are beautiful seasons to visit. The trees are either in bloom or in full autumn splendour, and the temperatures are moderate and comfortable. Because of these factors, though, these seasons are also the busiest. Summers in Virginia get hot and humid, so that could be a good off-peak time to visit if you enjoy warmer weather. If you don’t mind cooler conditions, though, consider winter. Most attractions are open year-round, snow is infrequent, and you’re likely to find good deals on accommodations.

Explore more of our road trips in the United States here >

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